Water-soluble dinitroarylamino-diarylamines and process of preparing same



Patented Apr, 16, 1929.

'UNITED STATES PATIENT OFFICE.

HERKANN WAGNER, OF BAD-SODEN-ON-THE-TAUNUS, GERMANY, ASSIGNOB TO GRAS- SELLI DYESTUFF CORPORATION, OF NEW YORK, N. Y., A CORPORATION 01' DELA- WARE.

WATER-SOLUBLE DINITROARYLAMINO-DIARYLAMINES AND PROCESS OF PREPARING SAME.

No Drawing. Applicationfiled October 10, 1927, Serial No. 225,395, and in Germany October 18, 1826.

OzN- R wherein R stands for one of the groups:

COOH, COO-metal, COO-alkyl,

aryl aryl CON SOz-N SOz-O-aryl,

alkyl alkyl but one R represents a nitro group.

The dyestuffs obtainable by my new process dye animal fibersyellow to reddish-brown tints and are for the most part particularly distinguished by the fact that they yield also fast dyeings on cellulose esters and cellulose ethers.

The condensation may be effected in any solvent, such as for instance in water, alcohol, pyridine, notrobenzene with or without the addition of an acid-binding agent, such as sodium acetate, chalk or the like.

The following examples serve to illustrate myinvention, but they are not intended to limit it thereto, the parts being parts by weight:

1. 27 8 parts of le-aminodiphenylamine-4J- methyl-Q-sulfonic acid are introduced into water, while stirring, and adding some chalk thereto. To the mass are then added 371,5 parts of SOz-ONa OIN NO:

OPE-O 2. Molecular proportions of 4-aminodiphenylamine-Q-sulfonic acid and 4-chlor-3.5- dinitro-l-benzoic acid are caused to act upon each other in the manner indicated in Example 1. The dyestutf thus obtained also crystallizes from water and is distinguished by the excellent fastncss of its yellowishbrown dyeings on wool. It has the following formula:

sor-om om N0:

doom

Instead of the 4-chlor-3.5-dinitro-1-benzoic acid there may also be used an ester, for I instance methyl ester.

3. The dyestulf prepared in the manner set forthin the foregoing examples from p-aminodiphenylamine and 4-chlor-3.5-dini- OCH:

OsN

OIN NO:

'dinitroarylamino-diarylamines, which consists in causing any p-aminodiphenylamine and a dinitrohalogenaryl of the following general formula:

Halogen Nb R.

tro-l-benzoic acid and having the following formula OaN NO:

OOH

or a metal salt thereof is particularly distinguished by its yielding an intense brown tint on acetyl cellulose. a

When proceeding in the manner indicated in the foregoing examples and working under similar conditions, the dyestuffs represented by-the following formulae are obtained COOH and so on OaNOC 00H wherein R stands for COOH, COO-metal, COO-alkyl,

but one B represents a nitro group, to act upon each other in the presence of a solvent.

2. The process of preparing water-soluble dinitroaryl-amino-diarylamines, which. consists in causing any p-aminodiphenyl-amine and a dinitrohalogenaryl of the following general formula:

Halogen NO R wherein R stands for COOH, COO-metal, COO-alkyl,

4 h oosm-o-m SOr-N 1 Y but one B represents 0. nitro group, to act upon each other in the presence of an acidbinding agent and, a solvent.

3. The process of preparing water-soluble dlnltroaryl-ammo-dlarylammes, which consists in causing any p-aminodiphenylamine and a dinitro-halogenaryl of the following general formula:

' Halogen NO NO:

wherein R stands for COOH, COO-metal, COO-alkyl,

to act upon each other in the presence of an acid-binding agent and a solvent.

4. The process of preparing water-soluble dinitroaryl-amino-diarylamines, which consists in causing any p-aminodiphenylamine and a dinitrohalogenaryl of the following general formula:

liialogen NO NO:

COOH

to act upon each other in the presence of an acid-binding agent and a solvent.

5. The process of preparing water-soluble dinitroarylamino-diarylamines. which consists in causing-any p-aminodiphenylamine and a dinitrohalogenaryl of the following general formula:

NOr- N02 Oi NH:

wherein X stands for hydrogen or a sulfo group and a dinitro-halogenaryl of the following general formula:

Halogen wherein R stands for COOH, COO-metal, COO-alkyl,

but one B represents a nitro group to act upon each other in the presence of an acid-binding agent and a solvent.

7. The process of preparing water-soluble dinitroaryl-amino-diarylalnines, which consists in causing a compound of the following formula:

wherein X stands for hydrogen or a sulfo group and a dinitro-halogenaryl of the following general formula:

Halogen NO -NO:

wherein R stands for COOH, COO-metal, COO-alkyl,

to act upon each other in the presence of an acid-binding agent and a solvent.

8. The process of preparing water-soluble dinitroaryl-amino-diarylamines, which consists in causing a compound of the following formula:

wherein X stands for hydrogen or a sulfo group and a dinitro-halogenaryl of the following general formula:

llIalogen COOH to act upon each other in the presence of an acid-binding agent and a solvent.

9. The process of preparingwater-soluble dinitroaryl-amino-diarylamines, which consists in causing compound of the following general formula wherein X stands for hydrogen or a sulfo group and a dinitro-halogenaryl of the following general formula:

. NO NO:

OOH

to act upon each other in the presence of anacid-binding agent and'a solvent.

10. The process of preparing water-soluble dinitroaryl-amine-diarylamines, which consists in causing 4-aminodiphenyl-amino-2- sulfonic acid of the following formula:

Gig-91m,

and a dinitro-halogenaryl of the following general formula:

Halogen NO R cap

and a (linitro-halogenaryl of the following general formula:

Halogen NO NO:

wherein R stands for COOH, COO-metal,

COO-alkyl,

alkyl 1 CON SOz-Oaryl, SOPN aryl alkyl to act upon each other in the presence of an acid-binding agent and a solvent.

12. The process of preparing water-soluble dinitroaryl-amino-diarylamines, which consists in causing 4-am1no-diphenyl-amine-2- s'ulfonic acid of the formula:

SOaOlI and a dinitro-halogenaryl of the following general formula: 7 Halogen (icon to act upon each other in the presence of an acid-binding agent and a solvent.

13. The process of preparing water-soluble dinitro-aryl-amino-'diai'ylamines, which consists in causing 4-amino-diphenylamine-2- sulfonic acid of the formula:

and a dinitro-haloge'naryl of the following sozon general formula to act upon each other in the presence of water and sodium acetate.

'14. As new products, the compounds of the following formula:

' NO: x x x x i I it B x f: x 2'1:

' wherein X stands for any substituent; R for COOH, COO-metal, COO-alkyl,

and one B represents a nitro group, said compounds bein water-soluble dyestuffs, dyeing animal fibers reddish-brown tints and partly giving fast dyeings on cellulose ethers and cellulose esters.

15. As new products, the compounds of the following formula:

wherein X stands for hydrogen or a sulfo group and R stands for CUOH, COO-metal, COU-alkyl,

R OzONa wherein R stands for COOH, COO-metal, COO-alkyl,

aryl

CON

but one B represents a nitro group, said compounds being water-soluble dyestuffs, dyeing animal fibers reddish-brown tints and partly giving fast dyeings on cellulose-ethers and cellulose-esters.

17. As new products, compounds which have most probably the following formula:

I|I RFQNO I H NO; SOzONa wherein R stands for COOH, COO-metal, CUO-alkyl,

said compounds being water-soluble dyestuffs, dyeing animal fibers reddish-brown tints and partly giving fast dyeings on cellulose-ethers and cellulose-esters.

18. As a new product, the compound which has most probably the following formula:

1 SOzONa being a dyestuif recrystallizable from Water which is distinguished by the great fastness of its yellowish-brown dyeing on Wool.

In testimony whereof, I affix my signature.

HERMANN WAGNER. 

